Decision-Making: The Virtues of Pessimism for an Optimist

September 17, 2020

Pessimists tend to get a bad rap. Pessimists are stereotyped as taking the fun out of every situation, always focusing on the negative, assuming failure is imminent, and believing hope is futile. Think Eeyore of Winnie the Pooh.

As with most entrepreneurs, my inclination is to be an eternal optimist. I attempt to find the positive in every situation and believe hidden opportunities abound, even in difficult times. I focus on the rewards and benefits more than I concern myself with the possibility of failure. 

It’s no surprise then that I absolutely believe optimism is an ingredient for success. But does this mean pessimism is a recipe for failure?

I have worked with a few strong-willed pessimists in my career and found it difficult. Possibly it was a clash of personalities that led to my frustration. But my experience is that their negative view of every situation reduced excitement and stifled creativity among a team. I also found pessimists to be of little value in offering solutions or useful advice to mitigate the negativity they describe.

However, I have discovered over the years that individuals with strong pessimistic “leanings,” can not only make significant contributions to the success of a team and a business but can be very successful personally as well.

An individual with pessimistic tendencies will typically warn of risk before identifying the reward. They will evaluate and outline the potential for failure. More importantly, they will caution an optimist like me to step back and properly assess a situation before making decisions or taking action. 

For this reason, I make an effort to involve one or more individuals with pessimistic tendencies in every significant decision I make. I want to hear their perspectives and concerns. I want to know why they take a negative perspective when I would take the positive. I want to understand the warnings and danger signs they have identified. 

To leverage the assistance of someone with pessimistic tendencies, and to best understand their pessimism related to a specific situation, I have found asking them the following questions is important.

1. What are your specific and primary concerns?  I am not interested in a broad-brushed pessimistic approach. I want to understand their specific concerns. Is it with particular individuals, onerous or one-sided requirements, financial terms, or other conditions not evident? I need them to be as detailed and specific as necessary about what they perceive as a potential problem.

2. Do you believe the level of risk is greater than the potential for the reward?  A risk-to-reward analysis is necessary when both are present in a decision. If you are an optimist, be aware that it’s easy to only see the potential for reward and not properly assess the underlying risk. I appreciate an individual who will properly evaluate risk from a pessimistic perspective to the point where they will argue that risk factors outweigh the reward. 

3. What would need to change for you to have a positive outlook?  A strong-willed pessimist will have trouble with this question. A person with pessimistic tendencies will not. They will be able to outline what specifically needs to change in a situation to remove their greatest concerns. By knowing this, I can now begin the process of developing possible solutions or negotiation points. 

Virtually every decision we make in business has an element of concern and risk. What is key, however, is in understanding and evaluating those concerns and risks. Having a person with pessimistic tendencies in the room when you make decisions or need advice can be a tremendous asset. But it is necessary to ask them the right questions, have them justify their pessimistic perspective, and to request their solutions. 

Optimistic individuals bring excitement and energy to the room. Pessimists can do the opposite and make everyone’s job more difficult. But successful leaders will make the best decisions by hearing and understanding the perspective of both the optimist and the pessimist.


Brian T. King is the founder/owner of multiple businesses encompassing design, construction, real estate and manufacturing. A well-respected construction industry CEO, Brian enjoys offering guidance to young professionals, rising managers and entrepreneurs on a variety of topics – from personal and professional growth, to work/life balance – through his bi-weekly blog, national podcasts, and speaking engagements around the country.

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